Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

I can’t believe it took me as long as it did to visit Chicago. I’m not a huge fan of freezing cold weather, especially when exploring a new city for the first time, so I knew I needed to visit in the warmer months. I kept visiting other places and Chicago kept getting pushed back. I finally decided that 2018 would be the year I would check this Midwest city off my list.  My husband and I planned a trip for Labor Day weekend so we could enjoy an extra night in the city. The weather was great and it was a perfect time to visit!

CHICAGO CITY GUIDE 

WHY VISIT

Chicago has tons of great attractions and things to do. Plus, they are known as a major foodie city with endless good restaurants to try. It has one of the busiest airports in the USA, making it easy to get to for a decent price, and it’s a walkable city, which makes it easy to explore. If you love a big city vibe, with great food, and tons to do you will love Chicago! 

Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

Chicago Outfit Recap. What to wear in Chicago. What to wear in Chicago in the summer. Summer in Chicago outfit ideas. Chicago outfit ideas. Chicago outfit inspo. What to wear in Chi Town. Chicago outfit inspiration. Chicago Outfits.

Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

WHERE TO STAY

We stayed at The Conrad hotel in the River North neighborhood of Chicago. This location was absolutely perfect and we could walk to a ton of the places we went, which is always a plus. We were right off of Michigan Avenue so any store you may want to visit is just around the corner. Plus, there are countless amazing restaurants within walking distance.

The Conrad was recommended to me several times and I am so glad we stayed there. We had a. big room with tons of space and a really comfortable King size bed. It also had a great city view! I loved the common areas of The Conrad and the rooftop. The lobby is actually located on one of the top floors, along with a bar that is a perfect place to grab a pre or post dinner cocktail. The rooftop restaurant, Noyane, is a great option for delicious food with a view, too.

The service at The Conrad was amazing and anything we need was taken care of promptly and with a smile. I’m not sure we could have been in a better location!

Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

WHERE TO EAT

My list of restaurants to try for Chicago is definitely one of the longest lists I have for any city. I asked for you all to send in recommendations on my Instagram stories on the ‘questions’ feature and I got a crazy number of responses. I love getting your input before traveling! I usually take the most recommended places and add them to my list, then check up on them myself by cross referencing them by looking at reviews, their websites, and other travel sites.  I’m going to include everywhere we went and then as usual, include places we didn’t make it to this time (never enough time for all the meals I want when traveling), but that I want to try next time.

  • RPM Italian: Added bonus because we saw Guiliana and Bill here when we came to eat. The Rancic’s are one of the owners of this little Italian spot that not only serves delicious food, but also has a great scene. We heard of other Italian restaurants that may have even better food, but the atmosphere here, especially for our first night in Chicago on a Friday night, was so much fun. We couldn’t decide what to get so we ordered several pasta to share and they were all so simple and so good.
  • Summer House Santa Monica: This adorable spot in Lincoln Park has a bright airy Cali vibe that is really refreshing. You feel like you are outside, but you’re covered by a clear tent in the event of inclement weather. Everything we tried here for brunch was delicious and we loved walking around Lincoln Park afterwards.
  • Maple and Ash: Amazing food, fun atmosphere.. what else do you need? This is a really cool steakhouse style restaurant that has a little of everything on the menu. We went on Saturday nigh and loved the vibe, as it was lively even late and a DJ was playing to keep a fun, but not disruptive scene. We went big and got a few appetizers including some French onion soup and then bae got Steak and Lobster (so I could steal some of the lobster) and I ordered like four different sides and a salad. Everything was so good and the service was amazing!
  • Lou Malnatis: For when you want the classic Chicago style deep dish pizza. Go early, because the wait will be long! It was really good though. I’m still of the mindset that regular pizza is better, but it’s great to experience deep dish where it all started. They have several locations, so we just picked the one closest to our hotel.

We have so many amazing places on the list for the next time we visit and I can’t wait to try them. It was super hard to narrow down where to eat, but I know I’ll be back so I have the below list ready to go whenever we do go back.

Brunch

  • Barrio Chicago: Mexican meets Japenese in a creative approach to food served up in a lively rustic-industrial spot that is perfect for brunch, lunch or a casual dinner.
  • Hampton Social River North: You may have seen the ‘rosé all day’ neon sign at this cute brunch spot. They have windows that open up and an outside area so you can enjoy the pretty days. They are known for delicious seafood and great, beach-inspired cocktails.
  • Bongo Room: This breakfast and brunch spot serves up seasonal and fresh food in a relaxed atmosphere.
  • M. Henry: This cute little spot is known for it’s classic American style breakfasts made using local and seasonal ingredients. It’s supposed to be quaint, relaxed, and delicious.
  • Kanela Breakfast Club: This is supposedly one of the best breakfast spots in town. The eggs Benedict is said to be one of the best ever and the red velvet french toast is reason enough to go.
  • Bar Sienna: This big, two-story restaurant serves up classic Italian fare, but I’ve heard their brunch is the best meal to go for. They have a patio and a lively bar scene, too.

Lunch

  • Big Star Chicago: Tacos, drinks, and honkey tonk. I definitely want to try out the Chicago taco scene, because these are supposed to be amazing, but it was hard for this Texan to have it on the top of the list for my first visit I’ll definitely be checking this place out during my next visit to see how they compare to ours in the Lone Star State!
  • Au Cheval Chica;go: Supposedly the best cheeseburger ever is made in this little diner style restaurant. There is almost always a few hour long wait, so go put your name down and grab some drinks nearby. We had some friends go here the weekend we were in town and they all said it lived up to the hype.
  • Portillo’s: For the world famous, Chicago hot dog.
  • Beatnik Chicago: This is a cute little cocktail bar, but they also have classic American food. The atmosphere is eclectic and fun and there is always a lively crowd to ensure a fun time.
  • Somerset: This good any-time-of-day restaurant at The Viceroy hotel has a yacht-club, chic feel. Their menu has classic-American style food and cocktails.
  • 3 Arts Cafe: This chic, stunning restaurant inside Restoration Hardware has an amazing menu and provides such a good setting for lunch or dinner. I am dying to go try the grilled cheese here and to take in the space, because I’ve heard its absolutely stunning.
  • Boka: One of Chicago’s most loved restaurants that serves up seasonal American food in a chic, candlelit garden patio scene.
  • Aba: This Mediterranean restaurant has a chic, outdoor rooftop patio that provides an always fun atmosphere.
  • Cafe Baba Reeba: This spot that is known for it’s Spanish style tapas. They serve up sangria in pitchers, so you know it will be a lively, fun scene any time.
  • Little Goat: A celebration of the classic diner serving classic American food with a creative spin in a chic, modern space.
  • Federales: Known for their Mexican-BBQ tacos, ceviche, and tequila, this fun warehouse setting is a great spot for a casual lunch. They have an outdoor beer garden, too making it a great spot to grab a day drink or some food.
  • Pub Royale: Indian food meets bar-pub food in a cute, but relaxed setting. This is such a cool concept and I’ve heard it’s not only so fun, but so good. Definitely on the list for something different to try on another visit.
  • Purple Pig: Delicious, Mediterranean inspired food known for it’s small plates and house cured meats. They have a great wine list and it’s an always lively spot.

Dinner

  • Ralph Lauren Bar and Grill: An upscale restaurant serving up American classics. I’ve heard so many people say this is their favorite spot for dinner in Chicago and I will absolutely be trying it for myself next time.
  • Noyane Chicago: This Japenese restaurant is on top of The Conrad and not only has beautiful views, but the menu looks so good.
  • Piccolo Sogno: I hear this is THE spot when you’re really focused on just getting amazing Italian food. The atmosphere is good, but probably described as less chic or sceney as RPM. I can’t wait to try this next time!
  • Joe’s Seafood: I’ve been to the original in Miami and this is another location that is supposedly just as amazing. This is an upscale classic seafood and steak restaurant with amazing service (the waiters are all in tuxedos) and absolutely delicious food.
  • Sunda: This modern Asian-fusion restaurant supposedly has great sushi. They also have creative, seasonally inspired craft cocktails.
  • Bavettes: This upscale steakhouse has a French inspired menu that is supposed to be delicious. The environment is cozy and romantic, making it a perfect date night spot.
  • Girl and the Goat: Globally inspired food served family style in a relaxed setting. Their menu looks amazing and has something for everyone.
  • GT Fish and Oyster: This is a popular seafood spot that serves shared plates paired with craft cocktails in a beautiful, modern and lively space.
  • Alinea: This has been named the best restaurant in the United States several times. They have an innovative approach to modern cuisine, which they serve up in several options of tasting menus so you can get a little of everything.

I know there are SO many amazing restaurants that there is no way I even got close to naming them all, so please send me any of your favorites I didn’t include so I can add them to the list and be sure I consider them for our next trip!

Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

Chicago Outfit Recap. What to wear in Chicago. What to wear in Chicago in the summer. Summer in Chicago outfit ideas. Chicago outfit ideas. Chicago outfit inspo. What to wear in Chi Town. Chicago outfit inspiration. Chicago Outfits.

Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

WHERE TO DRINK

  • ZBar Chicago: You can get good drinks and great views of the city from this rooftop terrace.
  • The Signature Room: View from the 95th floor of the John Hancock building. Pretty touristy and there will likely be a line. Make reservations if you can.
  • The Vig Chicago: Fun sports bar that plays 90s music and they have late night cookies. Yes, please. 
  • Old Town Ale House: If you’re a Bourdain fan, go here. It was on his Chicago Parts Unknown show and it is such a cool, cash only dive bar with tons of awesome history. 
  • Nico: This gorgeous hotel bar at The Thompson has a great, relaxed vibe as most Thompson hotels do. We went here before dinner one night. 
  • Cindys Rooftop: Yet another great rooftop bar. Can you ever have too many options with good views? Nope.
  • London House Chicago: I love hotel bars and this is a great option for an outdoor rooftop space with a fun vibe. 
  • Drum Bar: This speakeasy inspired bar at the Rafaello Hotel has craft cocktails and a laid back, cool atmosphere. 
  • Violet Hour: Great little speakeasy serving up artisan cocktails in the heart of Wicker Park.  
  • Gilt Bar: A cool, lounge style bar in the River North area that has good, creative cocktails.
  • J Parker: Hand crafted cocktails on top of Hotel Lincoln’s fun rooftop. 
  • RM Champagne Salon: Champagne, enough said. It’s located in the West Loop and has a great outdoor patio. 
  • Godfrey Rooftop: Drinks with a view in this chic rooftop bar on top of the Godfrey Hotel. 
  • Kingston Minds: Go here to hear live Blue’s music until 2AM. 
  • Green Door: The downstairs of this classic bar is supposed to have a great vibe
  • Blue Chicago: Go to this world-renonwed bar to hear the blues music
  • The Hang Up: Two floors are available with different vibes and music in this late night club. 

Chicago Outfit Recap. What to wear in Chicago. What to wear in Chicago in the summer. Summer in Chicago outfit ideas. Chicago outfit ideas. Chicago outfit inspo. What to wear in Chi Town. Chicago outfit inspiration. Chicago Outfits.

Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

Chicago Outfit Recap. What to wear in Chicago. What to wear in Chicago in the summer. Summer in Chicago outfit ideas. Chicago outfit ideas. Chicago outfit inspo. What to wear in Chi Town. Chicago outfit inspiration. Chicago Outfits.

Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

WHAT TO DO

Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

Sharing my Chicago city guide including where to stay in Chicago, where to eat in Chicago, where to drink, what to do, travel tips, and more in this easy travel guide to the Midwest's most popular city.

Chicago Outfit Recap. What to wear in Chicago. What to wear in Chicago in the summer. Summer in Chicago outfit ideas. Chicago outfit ideas. Chicago outfit inspo. What to wear in Chi Town. Chicago outfit inspiration. Chicago Outfits.

TRAVEL TIPS

  • Make reservations whenever possible! Almost all of the restaurants on our list took them and we were glad we made them! We were there on a holiday weekend so it may have been more busy than usual, but often times the restaurants were so busy we were seated a few minutes after our reservation time. Better safe than sorry to secure a table somewhere you really want to eat!
  • For places that don’t take reservations, Like Lou Malnati’s, go early to put your name down and be fine grabbing a drink somewhere near by. I always assume that places with consistently long waits are worth it.
  • Go early to tourist spots, like the Skydeck. There were lines to take photos in the glass overlook boxes and you only had a quick second or two in there, so go right when they open to avoid tons of people and snag any photo opps you want early.
  • Pack comfortable shoes for day time! You can definitely walk around a lot in Chicago and that is usually one of the best ways to see a city, so bring some shoes you don’t mind walking a bit in.

I hope my Chicago city guide helps you all when planning your next trip to the Windy City! We had such a great time and obviously have tons of great things to do the next time we go. If we missed any of your favorite places, please let us know so we can add it to the list and go when we visit again. Be sure to check out my Chicago outfit recap post to get some inspiration on what to wear for your trip!

In case you missed them, be sure to check out my Seattle city guide, my Oregon Coast travel guide, and if you’re headed abroad, my Paris city guide. XO

5 Comments

    • Work hard, play hard! Travel is one of my favorite things to do so I travel as much as I can in the summer when I’m off of work and then try to take about one trip a month. That would be so fun!!

      XO

  1. Great guide! I love how you broke down all of your restaurant recommendations! Atowle|https://formationvacations.com/

    • Thank you so much!! I always think that is helpful, so I’m glad you liked it.

      XO

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